(and Ken Jeong)

When you and your bodacious girlfriend (who, if you're lucky, looks like Kate Upton) jet off for a summer romp, pack a bag full of slimmed-down cords—and not much else. You'll look sexy, and she'll keep those starry eyes locked on you—even if you get photo-bombed by funnyman Ken Jeong

On him: Cords, $80 by Club Monaco. Sweater, $140 by Tommy Hilfiger. Watch by Smart Turnout. Necklace by Gregg Wolf.